Diisopropylethylamine → Methyl cis(+/-)-2-chloro-6-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)pyridine-4-carboxylate

HRID 43791Notes

Reaction equation

HRID 43791 reaction equation
Cl.[Cl:2][C:3]1[N:4]=[C:5]([C:10]([NH:12][C@H:13]2[CH2:18][CH2:17][NH:16][CH2:15][C@H:14]2[O:19][CH3:20])=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9].[Cl:21][C:22]1[CH:27]=[C:26]([C:28]([O:30][CH2:31]C)=[O:29])[CH:25]=[C:24](Cl)[N:23]=1.C(N(C(C)C)CC)(C)C>>[Cl:21][C:22]1[CH:27]=[C:26]([C:28]([O:30][CH3:31])=[O:29])[CH:25]=[C:24]([N:16]2[CH2:17][CH2:18][C@H:13]([NH:12][C:10]([C:5]3[NH:6][C:7]([CH2:8][CH3:9])=[C:3]([Cl:2])[N:4]=3)=[O:11])[C@H:14]([O:19][CH3:20])[CH2:15]2)[N:23]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 948232,6-Dichloro-isonicotinic acid ethyl esterHCID 86648695cis(+/-)-4-Chloro-5-ethyl-N-(3-methoxypiperidin-4-yl)-1H-imidazole-2-carboxamide hydrochloride

Product 1

HCID 86648741Methyl cis(+/-)-2-chloro-6-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)pyridine-4-carboxylate

Procedure

The same operation as in Example (158a) was performed using cis(±)-4-chloro-5-ethyl-N-(3-methoxypiperidin-4-yl)-1H-imidazole-2-carboxamide hydrochloride obtained in Example (159a) (107 mg, 0.33 mmol), ethyl 2,6-dichloro-pyridine-4-carboxylate (65 mg, 0.32 mmol) and diisopropylethylamine (122 mg, 0.95 mmol), to obtain the title compound as a yellow brown oily substance.

Sources & evidence

ORD record
ord-6b856fc8b9f14acdae71c2e7211112fe
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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